Previous research by Vitton & Wasonga (2009) and Strenth (2013) found public school K-12 principals struggling in the moral reasoning and decision-making measures of the second Defining Issues Test (“DIT-2”). In response to these studies, this research sought to collect, to examine, and to compare DIT-2 data for educational leaders at various stages of the principalship track in an effort to determine and/or to isolate the locus of principals’ reported underperformance. The moral reasoning and decision-making of regular-education K-12 public school principals and assistant principals in Florida, and current master’s degree students in educational leadership programs at a large public Florida university were measured and compared.